US4456554A - Ammonium compounds - Google Patents

Ammonium compounds Download PDF

Info

Publication number
US4456554A
US4456554A US06/417,828 US41782882A US4456554A US 4456554 A US4456554 A US 4456554A US 41782882 A US41782882 A US 41782882A US 4456554 A US4456554 A US 4456554A
Authority
US
United States
Prior art keywords
alkyl
designates
formula
methyl
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US06/417,828
Inventor
Klaus Walz
Karl Schafer
Gunther Hoffarth
Hans Schulze
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6141985&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US4456554(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bayer AG filed Critical Bayer AG
Assigned to BAYER AKTIENGESELLSCHAFT; A CORP. reassignment BAYER AKTIENGESELLSCHAFT; A CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HOFFARTH, GUNTHER, SCHAFER, KARL, SCHULZE, HANS, WALZ, KLAUS
Application granted granted Critical
Publication of US4456554A publication Critical patent/US4456554A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof

Definitions

  • the invention relates to new ammonium compounds of the formula ##STR3## in which R and R 1 designate C 1 -C 21 -alkyl or C 2 -C 21 -alkenyl,
  • R' designates hydrogen or C 1 -C 4 -alkyl
  • R 2 designates C 1 -C 4 -alkyl or hydroxy-C 1 -C 4 -alkyl
  • R 3 designates hydrogen or C 1 -C 4 -alkyl
  • A.sup. ⁇ represents an anion of the formula ##STR4## in which R 4 designates hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and
  • R 5 designates C 1 -C 4 -alkyl or C 1 -C 4 -hydroxyalkyl
  • Preferable anions A.sup. ⁇ are: ##STR5##
  • Ammonium compounds of the formula I are prepared by reacting esters of the formula ##STR6## in which
  • R, R', R 1 and R 2 have the meanings indicated in the formula I
  • R 3 , R 4 and R 5 have the meanings indicated in the formulae (I) and (II).
  • the new compounds are obtained here as solid or pasty products which are readily soluble or dispersible in water.
  • esters of the formula ##STR8## are obtained by reacting esters of the formula ##STR8## with trimethyl phosphate, triethyl phosphate, dimethyl methanephosphonate or diethyl ethanephosphonate, but in particular with dimethyl phosphite or diethyl phosphite.
  • Esters of the formulae III or V can be prepared in a manner which is in itself known, for example by reaction of 2 mols of a corresponding carboxylic acid or of its low alkyl ester with 1 mol of a compound of the formula ##STR9## in which
  • R' and R 2 have the meanings indicated in the formula I
  • the amine can first be reacted with one mol of a carboxylic acid and the product then reacted with one mol of another carboxylic acid.
  • carboxylic acids are not only pure acids, such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid or linoleic acid, but also, if appropriate, acid mixtures, such as possibly hydrogenated fatty acid mixtures on which natural fats are based or fractions of such fatty acid mixtures.
  • the new ammonium compounds are suitable for use as softeners for fibre materials, such as textile fibre materials made of synthetic fibres, for example of polyester, polyacrylonitrile or polyamide fibres, and, in particular, of cotton or regenerated cellulose fibres. They are also suitable for use as softening agents for paper.
  • the new compounds are applied to fibre materials in a manner which is customary for softeners, for example by the exhaust method from a long liquor.
  • 0.1 g to 10 g of the new compounds per liter of water are dissolved or dispersed.
  • amounts of 5-25 g per liter of liquor are advantageously used.
  • 35 parts of dimethyl methanephosphonate are added to 165 parts of an ester prepared analogously to Example 1 from 1 mol of stearic acid and 1 mol of lauric acid with 1 mol of N-methyl-N,N-diethanolamine, and the mixture is stirred for 6 hours at 140° C.
  • the result is a water-soluble product which, at room temperature, solidifies to give a pasty material.
  • the surface tension of an 0.5% strength aqueous solution at 20° C. is 35.9 mN.m -1 .
  • Example 1 0.5% of the product of Example 1 (relative to the weight of the goods) is dissolved 1:10 in water, and the solution is added to an aqueous liquor, the amount of which, in proportion to the weight of the goods, is 1:20.
  • the textile material used is cotton terry towelling having a weight per square meter of 100 g/m 2 .
  • the treatment temperature is 40° C., and the treatment time is 30 minutes.
  • the material is then squeezed, in a pad mangle, down to a liquor pick-up of 100% and dried 2-3 minutes at 120° C. The result is a pleasant, soft handle.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Ammonium compounds of the formula ##STR1## in which R and R1 designate C1 -C21 -alkyl or C2 -C21 -alkenyl,
R' designates hydrogen or C1 -C4 -alkyl,
R2 designates C1 -C4 -alkyl or hydroxy-C1 -C4 -alkyl,
R3 designates hydrogen or C1 -C4 -alkyl and
A.sup.⊖ represents an anion of the formula ##STR2## in which R4 designates hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxy and
R5 designates C1 -C4 -alkyl or C1 -C4 -hydroxyalkyl,
a process for their preparation and their use as softeners for fibre materials.

Description

The invention relates to new ammonium compounds of the formula ##STR3## in which R and R1 designate C1 -C21 -alkyl or C2 -C21 -alkenyl,
R' designates hydrogen or C1 -C4 -alkyl,
R2 designates C1 -C4 -alkyl or hydroxy-C1 -C4 -alkyl,
R3 designates hydrogen or C1 -C4 -alkyl and
A.sup.⊖ represents an anion of the formula ##STR4## in which R4 designates hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxy and
R5 designates C1 -C4 -alkyl or C1 -C4 -hydroxyalkyl,
a process for their preparation and their use as softeners for fibre materials.
The following meanings of individual substituents are preferable:
R or R1 C11 -C21 -alkyl or C11 -C21 -alkenyl; R' hydrogen or methyl; R3 methyl or ethyl; R4 hydrogen, methyl, ethyl, methoxy or ethoxy; and R5 methyl or ethyl.
Those compounds of the formula I are particularly preferable in which R2 designates methyl and R3 designates hydrogen, methyl or ethyl.
Preferable anions A.sup.⊖ are: ##STR5##
Ammonium compounds of the formula I are prepared by reacting esters of the formula ##STR6## in which
R, R', R1 and R2 have the meanings indicated in the formula I
at temperatures of about 50° to about 200° C., preferably at 100°-150° C., with compounds of the formula ##STR7## in which
R3, R4 and R5 have the meanings indicated in the formulae (I) and (II).
The new compounds are obtained here as solid or pasty products which are readily soluble or dispersible in water.
Preferable compounds are obtained by reacting esters of the formula ##STR8## with trimethyl phosphate, triethyl phosphate, dimethyl methanephosphonate or diethyl ethanephosphonate, but in particular with dimethyl phosphite or diethyl phosphite.
Esters of the formulae III or V can be prepared in a manner which is in itself known, for example by reaction of 2 mols of a corresponding carboxylic acid or of its low alkyl ester with 1 mol of a compound of the formula ##STR9## in which
R' and R2 have the meanings indicated in the formula I
at temperatures of 100° to 180° C., water formed during the reaction or the lower alcohol being continuously removed from the reaction mixture. For the case that R≠R1 the amine can first be reacted with one mol of a carboxylic acid and the product then reacted with one mol of another carboxylic acid.
Possible examples of carboxylic acids are not only pure acids, such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid or linoleic acid, but also, if appropriate, acid mixtures, such as possibly hydrogenated fatty acid mixtures on which natural fats are based or fractions of such fatty acid mixtures.
The new ammonium compounds are suitable for use as softeners for fibre materials, such as textile fibre materials made of synthetic fibres, for example of polyester, polyacrylonitrile or polyamide fibres, and, in particular, of cotton or regenerated cellulose fibres. They are also suitable for use as softening agents for paper.
The new compounds are applied to fibre materials in a manner which is customary for softeners, for example by the exhaust method from a long liquor. For this purpose, 0.1 g to 10 g of the new compounds per liter of water are dissolved or dispersed. On application by the pad method, amounts of 5-25 g per liter of liquor are advantageously used.
In the examples which follow, parts are parts by weight.
EXAMPLE 1
241 parts of hydrogenated coconut fatty acid and 22 parts of stearic acid are dissolved in 60 parts of toluene, 75 parts of N-methyl-N,N-diethanolamine are added, and the mixture is heated to 130°-140° C., water formed being distilled off azeotropically.
After toluene has been distilled off, 65 parts of dimethyl phosphite are added to the resulting ester, and the mixture is heated for 4-5 hours at 140° C. After cooling down, the mixture is obtained as a viscous liquid which gives a slightly turbid solution in water. The surface tension of an 0.5% strength aqueous solution at 20° C. is 31.4 mN.m-1.
EXAMPLE 2
35 parts of dimethyl methanephosphonate are added to 165 parts of an ester prepared analogously to Example 1 from 1 mol of stearic acid and 1 mol of lauric acid with 1 mol of N-methyl-N,N-diethanolamine, and the mixture is stirred for 6 hours at 140° C. The result is a water-soluble product which, at room temperature, solidifies to give a pasty material. The surface tension of an 0.5% strength aqueous solution at 20° C. is 35.9 mN.m-1.
EXAMPLE 3
0.5% of the product of Example 1 (relative to the weight of the goods) is dissolved 1:10 in water, and the solution is added to an aqueous liquor, the amount of which, in proportion to the weight of the goods, is 1:20.
The textile material used is cotton terry towelling having a weight per square meter of 100 g/m2. The treatment temperature is 40° C., and the treatment time is 30 minutes. The material is then squeezed, in a pad mangle, down to a liquor pick-up of 100% and dried 2-3 minutes at 120° C. The result is a pleasant, soft handle.
EXAMPLE 4
15 g of the ammonium compound prepared according to Example 2 are dissolved 1:10 in water at 40° C. The solution is made up to 1 liter with water. Cotton terry towelling having a square meter weight of 180 g/m2 is dipped into the liquor and squeezed off, in a pad mangle, down to a liquor pick-up of 90%. The material is then dried for 2-3 minutes at 120° C. The result is terry towelling fabric having a pleasant, soft handle.

Claims (7)

We claim:
1. Ammonium compounds of the formula ##STR10## in which R and R1 designate C1 -C21 -alkyl or C2 -C21 -alkenyl,
R' designates hydrogen or C1 -C4 -alkyl,
R2 designates C1 -C4 -alkyl or hydroxy-C1 -C4 -alkyl,
R3 designates hydrogen or C1 -C4 -alkyl and
A.sup.⊖ represents an anion of the formula ##STR11## in which R4 designates hydrogen, C1 -C4 -alkyl or C1 -C4 -alkoxy and
R5 designates C1 -C4 -alkyl or C1 -C4 -hydroxyalkyl.
2. Compounds according to claim 1, in which, in the formula I,
R and R1 designate C11 -C21 -alkyl or C11 -C21 -alkenyl,
R' designates hydrogen or methyl,
R2 designates C1 -C4 -alkyl or hydroxy-C1 -C4 -alkyl,
R3 designates methyl or ethyl,
R4 designates hydrogen, methyl, ethyl, methoxy, or ethoxy and
R5 designates methyl or ethyl.
3. Compounds according to claims 1 and 2, in which
R2 designates methyl and
R3 designates hydrogen, methyl or ethyl.
4. Compounds according to claims 1 to 3, characterised in that A.sup.⊖ represents a ##STR12##
5. Ammonium compounds which can be obtained by reacting compounds of the formula ##STR13## with trimethyl phosphate, triethyl phosphate, dimethyl methanephosphonate or diethyl ethanephosphonate, but, in particular, with dimethyl phosphite or diethyl phosphite.
6. Process for preparing ammonium compounds according to claim 1, characterized in that esters of the formula ##STR14## in which R, R', R1 and R2 have the meanings indicated in claim 1
at temperatures of about 50° to about 200° C. with compounds of the formula ##STR15## in which R3, R4 and R5 have the meanings indicated in claim 1.
7. Use of compounds according to claims 1 to 5, as softeners for fibre materials.
US06/417,828 1981-09-17 1982-09-13 Ammonium compounds Expired - Lifetime US4456554A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813137043 DE3137043A1 (en) 1981-09-17 1981-09-17 AMMONIUM COMPOUNDS
DE3137043 1981-09-17

Publications (1)

Publication Number Publication Date
US4456554A true US4456554A (en) 1984-06-26

Family

ID=6141985

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/417,828 Expired - Lifetime US4456554A (en) 1981-09-17 1982-09-13 Ammonium compounds

Country Status (4)

Country Link
US (1) US4456554A (en)
EP (1) EP0075168B1 (en)
JP (1) JPS5862142A (en)
DE (2) DE3137043A1 (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675131A (en) * 1984-12-12 1987-06-23 Interox(Societe Anonyme) Organic quaternary ammonium compounds and process for the preparation thereof
US4767547A (en) * 1986-04-02 1988-08-30 The Procter & Gamble Company Biodegradable fabric softeners
US4830771A (en) * 1987-06-19 1989-05-16 Huels Aktiengesellschaft Process for the preparation of trialkanolamine di(fatty acid) esters, and the use thereof for softening fabrics
US4865768A (en) * 1986-01-23 1989-09-12 Henkel Kommanditgesellschaft Auf Aktien Phosphoric acid salt of the reaction product of a mono-carboxylic acid with a polyamine
US5019281A (en) * 1988-12-17 1991-05-28 Ciba-Geigy Corporation Hydrophilic softhand agency for fibrous materials and use thereof
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5552137A (en) * 1994-08-05 1996-09-03 Witco Corporation Biodegradable quaternary hair conditioners
US5643865A (en) * 1994-05-18 1997-07-01 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing quaternary ammonium compounds with short fatty acid alkyl chains
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US5919750A (en) * 1997-07-24 1999-07-06 Akzo Nobel Nv Fabric softener composition
US6166232A (en) * 1996-06-12 2000-12-26 Akzo Nobel Nv Process for producing ester quats
EP1964833A1 (en) * 2007-03-02 2008-09-03 Cognis IP Management GmbH Asymmetric cationic surfactants
US20090318315A1 (en) * 2008-06-24 2009-12-24 Brine-Add Fluids Ltd. Gelled hydrocarbons for oilfield processes and methods of use

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3710064A1 (en) * 1987-03-27 1988-10-06 Hoechst Ag METHOD FOR THE PRODUCTION OF QUATERNAUS ESTERAMINES AND THEIR USE
DE3807068A1 (en) * 1988-03-04 1989-09-14 Henkel Kgaa QUATED IMIDAZOLINIUM PHOSPHATE
ES2021900A6 (en) * 1989-07-17 1991-11-16 Pulcra Sa Process for preparing quaternary ammonium compounds.
FR2685649B1 (en) * 1991-12-31 1994-09-23 Stepan Europe SURFACTANTS BASED ON QUATERNARY AMMONIUM COMPOUNDS, PREPARATION METHOD, DERIVATIVE BASES AND SOFTENING COMPOSITIONS.
DE69214618T2 (en) * 1991-12-31 1997-02-20 Stepan Europe Quaternary ammonium surfactants, processes for their preparation, bases and their plasticizers
FR2688419B1 (en) * 1992-03-12 1994-07-08 Stepan Europe SURFACTANT BASE COMPRISING A CATIONIC QUATERNARY AMMONIUM COMPOUND AND A COMPOUND AS A SOLVENT AND SOFTENING COMPOSITION COMPRISING SUCH A BASE.
FR2693665B1 (en) * 1992-07-17 1994-09-23 Stepan Europe Cationic surfactant compositions, based on mono or polyalkyl ester and / or amido ammonium, and methods for their preparation.
US5264082A (en) * 1992-04-09 1993-11-23 Procter & Gamble Company Soft absorbent tissue paper containing a biodegradable quaternized amine-ester softening compound and a permanent wet strength resin
US5262007A (en) * 1992-04-09 1993-11-16 Procter & Gamble Company Soft absorbent tissue paper containing a biodegradable quaternized amine-ester softening compound and a temporary wet strength resin
DE4243547C2 (en) * 1992-12-22 1994-10-20 Henkel Kgaa Quaternized fatty acid triethanolamine ester salts
ES2097476T3 (en) * 1993-09-17 1997-04-01 Stepan Europe SURFACE BASE WHICH INCLUDES A CATIONIC COMPONENT OF QUATERNARY AMMONIUM AND A COMPOUND AS A SOLVENT AND SOFTENING COMPOSITION THAT INCLUDES SUCH BASE.
DE4334367A1 (en) * 1993-10-08 1995-04-13 Henkel Kgaa Process for the production of service papers with improved soft hand

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US30748A (en) * 1860-11-27 Improvement in cultivators
US3539601A (en) * 1967-07-12 1970-11-10 Swift & Co Fatty amido amines
US4197350A (en) * 1977-10-25 1980-04-08 Hoechst Aktiengesellschaft Quaternized amine-amide condensation products and their use in oil-containing fiber preparations
EP0021546A2 (en) * 1979-07-02 1981-01-07 Akzo N.V. Quaternary ammonium compounds as fabric-softening agents
US4264516A (en) * 1977-08-01 1981-04-28 Ciba-Geigy Corporation Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
EP0029172A1 (en) * 1979-11-14 1981-05-27 Hoechst Aktiengesellschaft Alkylphosphonic acid half-ester salts, their preparation and their use as sizing agents in textile fibres

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US30748A (en) * 1860-11-27 Improvement in cultivators
US3539601A (en) * 1967-07-12 1970-11-10 Swift & Co Fatty amido amines
US4264516A (en) * 1977-08-01 1981-04-28 Ciba-Geigy Corporation Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof
US4197350A (en) * 1977-10-25 1980-04-08 Hoechst Aktiengesellschaft Quaternized amine-amide condensation products and their use in oil-containing fiber preparations
EP0021546A2 (en) * 1979-07-02 1981-01-07 Akzo N.V. Quaternary ammonium compounds as fabric-softening agents
EP0029172A1 (en) * 1979-11-14 1981-05-27 Hoechst Aktiengesellschaft Alkylphosphonic acid half-ester salts, their preparation and their use as sizing agents in textile fibres

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4675131A (en) * 1984-12-12 1987-06-23 Interox(Societe Anonyme) Organic quaternary ammonium compounds and process for the preparation thereof
US4865768A (en) * 1986-01-23 1989-09-12 Henkel Kommanditgesellschaft Auf Aktien Phosphoric acid salt of the reaction product of a mono-carboxylic acid with a polyamine
US4767547A (en) * 1986-04-02 1988-08-30 The Procter & Gamble Company Biodegradable fabric softeners
US4830771A (en) * 1987-06-19 1989-05-16 Huels Aktiengesellschaft Process for the preparation of trialkanolamine di(fatty acid) esters, and the use thereof for softening fabrics
US5019281A (en) * 1988-12-17 1991-05-28 Ciba-Geigy Corporation Hydrophilic softhand agency for fibrous materials and use thereof
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
US5562849A (en) * 1993-03-01 1996-10-08 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5574179A (en) * 1993-03-01 1996-11-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains
US5643865A (en) * 1994-05-18 1997-07-01 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing quaternary ammonium compounds with short fatty acid alkyl chains
US5610187A (en) * 1994-08-05 1997-03-11 Witco Corporation Biodegradable quaternary hair and skin conditioners
US5552137A (en) * 1994-08-05 1996-09-03 Witco Corporation Biodegradable quaternary hair conditioners
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
US6770608B2 (en) 1996-05-03 2004-08-03 Akzo Nobel N.V. High di(alkyl fatty ester) amines and quaternary ammonium compounds derived therefrom
US5916863A (en) * 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
US6004913A (en) * 1996-05-03 1999-12-21 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compound in esteramine from triethanolamine
US6037315A (en) * 1996-05-03 2000-03-14 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions
US6323167B1 (en) 1996-05-03 2001-11-27 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions
US6166232A (en) * 1996-06-12 2000-12-26 Akzo Nobel Nv Process for producing ester quats
US5919750A (en) * 1997-07-24 1999-07-06 Akzo Nobel Nv Fabric softener composition
EP1964833A1 (en) * 2007-03-02 2008-09-03 Cognis IP Management GmbH Asymmetric cationic surfactants
US20080214850A1 (en) * 2007-03-02 2008-09-04 Joaquin Bigorra Llosas Asymmetric cationic surfactants
US7786319B2 (en) 2007-03-02 2010-08-31 Cognis Ip Management Gmbh Asymmetric cationic surfactants
US20090318315A1 (en) * 2008-06-24 2009-12-24 Brine-Add Fluids Ltd. Gelled hydrocarbons for oilfield processes and methods of use
US7947631B2 (en) 2008-06-24 2011-05-24 Brine-Add Fluids Ltd. Gelled hydrocarbons for oilfield processes and methods of use
US20110190172A1 (en) * 2008-06-24 2011-08-04 Brine-Add Fluids Ltd. Gelled hydrocarbons for oilfield processes and methods of use
US8367590B2 (en) 2008-06-24 2013-02-05 Engenium Chemicals Corp. Gelled hydrocarbons for oilfield processes and methods of use

Also Published As

Publication number Publication date
DE3269405D1 (en) 1986-04-03
EP0075168A1 (en) 1983-03-30
JPH0319218B2 (en) 1991-03-14
EP0075168B1 (en) 1986-02-26
DE3137043A1 (en) 1983-03-24
JPS5862142A (en) 1983-04-13

Similar Documents

Publication Publication Date Title
US4456554A (en) Ammonium compounds
US3972855A (en) Quaternary ammonium compounds and treatment of plastic and other materials therewith
EP0453406B1 (en) 5,5-Bis(perfluoroalkylheteromethyl)-2-hydroxy-2-oxo-1,3,2-dioxaphosphorinanes, derived acyclic phosphorus acids and salts or esters thereof
US2487899A (en) Process of wax sizing papermaking fibers using a cationic surface active agent
US4237064A (en) Process for preparing quaternary ammonium compositions
US4153561A (en) Conditioning agent
US4104175A (en) Aqueous solutions of quaternary ammonium compounds
US4119789A (en) Flame retardant compositions
US3900327A (en) Flame retardant cellulosic materials
US5576470A (en) Polyol esters of ether carboxylic acids and fiber finishing methods
US2970158A (en) Surface active agents
US5314718A (en) Fiber finishing methods
US4197350A (en) Quaternized amine-amide condensation products and their use in oil-containing fiber preparations
US4342706A (en) Benzene sulfonate quaternary ammonium salts
US5240743A (en) Fiber finishing methods
US4399044A (en) Textile softening composition
US2488515A (en) Utilization of waste wax paper
US2407703A (en) Amino amide compounds
US4376736A (en) Rate and yield enhancement in the preparation of ethoxylated quaternary ammonium borates using ethylene glycol
US3634117A (en) A textile material coated with an ammonium dialkyl phosphate antistatic agent
US4001285A (en) Amidopolyaminesulfonates
US4515723A (en) Quaternary N-alkyl-N,N',N'-polyoxyalkyl-α,ω-diamino-alkylene fatty acid esters, and their use
US3875197A (en) Amido-methyl-polyglycol formals
CA1163275A (en) Quaternary alkylamino-di-alkylcarboxylic acid di- esters, process for their manufacture and their use
US3997698A (en) Process of sizing fabrics and threads with triamides

Legal Events

Date Code Title Description
AS Assignment

Owner name: BAYER AKTIENGESELLSCHAFT; LEVERKUSEN, GERMANY A G

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:WALZ, KLAUS;SCHAFER, KARL;HOFFARTH, GUNTHER;AND OTHERS;REEL/FRAME:004045/0425

Effective date: 19820903

Owner name: BAYER AKTIENGESELLSCHAFT; A CORP., GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WALZ, KLAUS;SCHAFER, KARL;HOFFARTH, GUNTHER;AND OTHERS;REEL/FRAME:004045/0425

Effective date: 19820903

STCF Information on status: patent grant

Free format text: PATENTED CASE

CC Certificate of correction
FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12